Indole → HCID 68487547, compound

HRID 1178732Notes

Reaction equation

HRID 1178732 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][CH:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[C:15]1([C:20](Cl)=[O:21])[S:19][CH:18]=[CH:17][CH:16]=1.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1>>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[N:6]2[C:20]([C:15]2[S:19][CH:18]=[CH:17][CH:16]=2)=[O:21])=[CH:24]1

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 789282-Thiophenecarbonyl chloride

Product 1

HCID 68487547HCID 68487547, compound

Procedure

[6-(1H-Indol-3-yl)-6H-phenanthridin-5-yl]-thiophen-2-yl-methanone was prepared from phenanthridine, 2-thenoyl chloride, and indole according to GP 2. Yield, 17%. 1H-NMR (CD3OD): δ=6.17 (d, J=0.9 Hz, 1H), 6.67 (d, J=7.9 Hz, 1H), 6.84-6.89 (m, 2H), 6.91 (td, J=3.8 Hz, J=1.1 Hz, 1H), 7.02-7.11 (m, 2H), 7.18-7.24 (m, 2H), 7.26 (s, 1H), 7.38-7.46 (m, 2H), 7.50-7.56 (m, 2H), 7.93 (dd, J=7.9 Hz, J=1.3 Hz, 1H), 7.97-8.01 (m, 1H), 8.06 (d, J=7.9 Hz, 1H); (+)-ESI-MS: m/z=407 [M+H]+, 290 [M-indole+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-18a7fbeb90cf4170bbe34c1537a904fa
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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